Infrared Spectroscopy of Organic

Compounds
Ashley F. Aquino, Daniel Gene B. Vicente, John Jerald B. Villamanca,
& Alicia Monique C. Yamamoto
College of Science, University of Santo Tomas, Manila, Philippines

Abstract

Infrared (IR) spectroscopy is one of the most common and widely used
spectroscopic techniques employed mainly by inorganic and organic chemists due to its
usefulness in determining structures of compounds and identifying them. In this
experiment, we focused on learning IR spectroscopic methods to characterize functional
groups. The results of IR peaks based on the spectra were recorded. There were 5 known
samples and 5 unknown. The 5 known samples observed were hexane, isoamyl alcohol,
cyclohexanol, cyclohexanone, and tuolene.

Introduction

Spectroscopy is the study of matter and its interaction with electromagnetic

radiation. All matter contains molecules that have bonds that are continually vibrating and
moving around. These bonds can vibrate with stretch motions or bend motions. A
technique that is very frequently used to assist in the identification of unknown compounds
uses infrared (IR) light, a form of electromagnetic radiation. Chemical compounds have
different chemical properties due to the presence of different functional groups.
A machine called an IR Spectrometer passes infrared radiation through a sample
of an unknown compound and uses a detector to plot percent transmission of the radiation
through the molecule versus the wavenumber of the radiation. A downward peak on the
plot represents absorption at a specific wavenumber. IR spectroscopy is useful in
determining chemical structure because energy that corresponds to specific values allows
us to identify various functional groups within a molecule.
To generate the IR spectrum, different frequencies of infrared light are passed
through a sample, and the transmittance of light at each frequency is measured. The
transmittance is then plotted versus the frequency of the light (which is presented in the
somewhat unusual units of cm-1).
 Functional groups are the portions in an organic molecule that dictate how the
molecule will react. Different functional groups produce bond absorptions at different
locations and intensities on the IR spectrum. Recognizing where the absorptions
generated by the common functional groups occur will help you to interpret IR spectra.
This table lists the locations and intensities of absorptions produced by typical functional
groups.

Results and Discussion

Infrared spectrometer has the capability of scanning and detecting the functional
groups that compose a certain compound. It sends a beam of infrared light, wherein some
of them are absorbed and some of them are transmitted. To examine functional groups, this
experimental study involved the utilization of the transmitted rays from the sent beam of
light. The said transmitted rays created a spectrum that can be interpreted by investigating
the region where they are located in. However, the region of fingerprint couldn't be used in
interpreting the data gathered.

Fig. 1. The spectra displayed by Infrared Spectrometer when it scanned hexane (left) and
UNKNOWN C compound (right).

Hexane. After preparing and calibrating the instrument, a drop of hexane, (CH2)5CO
was inputted in the scanning region of spectrometer. The instrument then scanned the
compound and displayed a spectrum (shown in Fig. 1). The peaks in the spectrum indicated
a sharp signal with strong intensity frequency along 2850 cm -1 and 2975 cm-1, which is in
lieu with the standard frequency for the alkane (C-H) groups. (literature value 2960 cm-1 -
2850 cm-1 [World Wide Web]). A similar result was obtained when UNKNOWN C
compound was scanned by the instrument.
Fig. 2. The spectra displayed by Infrared Spectrometer when it scanned cyclohexanol
(left) and UNKNOWN D compound (right).

Cyclohexanol. A drop of cyclohexanol, C6H12O was as also examined. The

Infrared spectroscopy scanned the drop and printed a spectrum (shown in Fig. 2). There
were two distinct peaks shown in the spectrum. The leftmost peak showed a broad signal
with strong intensity between 3400 – 3200 cm-1. This indicates that it could be inferred to
bear a hydroxyl group (O-H) (literature value 3640-3160 cm-1).

On the other hand, another peak displayed a frequency of sharp signal with strong
intensity along 2950 - 2800 cm-1. This signifies an alkane group (C-H) (literature value 2969-
2850 cm-1 ).

There were similar results obtained when UNKNOWN D, as shown on the right side
of figure 2, was scanned by the spectroscopy. When it was compared, it showed
frequencies consistent with each other.

Fig. 3. The spectra displayed by Infrared Spectrometer when it scanned isoamyl (left) and
UNKNOWN E compound (right).

Isoamyl. A drop of isoamyl, C5H12O was examined as well. Using Infrared

spectroscopy, the drop was scanned and resulting data was calculated (shown in Fig. 3).
The spectrum displayed one strong peak and a broad spike. The left spike, which is broad
with medium intensity, showed a frequency of 3400 - 3100 cm-1. Additionally, the second
peak displayed in fig. 3 displayed frequency at about 2950 - 2800 cm-1.

Much like the previous compound, cyclohexanol, the peak of both compound has a
frequency of, 3400 - 3200 cm-1 could be interpreted as compounds with a hydroxyl group
(O-H) (literature value 3640-3160 cm-1). On the other hand, the second peak indicates the
presence of an alkane group (C-H) (literature value 2969-2850 cm-1). There were
congruent results obtained when UNKNOWN D was scanned by the IR spectroscopy.

Fig. 4. The spectra displayed by Infrared Spectrometer when it scanned toluene (left) and
UNKNOWN A compound (right).

The infrared spectroscopy of the Toluene (C7H8), as shown in Figure 4, shown

frequencies along the range of 3100 cm-1, indicating there was an absorption of C-H bond
due to a sharp signal with its peak at an estimate 2950 cm-1. It also had a sharp signal and
weak transmittance with weak intensity along the absorption 3000 cm -1. Additionally, the
frequencies along the 2950-2800 cm-1 y-axis had a sharp signal with weak intensity, also
indicating a C-H bond.

Also, there were other frequencies detected along 1500 cm -1 and 1600 cm-1. Both
had a sharp signal with medium intensity. This indicates a C=C bond, which may be
interpreted as presence of an aromatic ring. Aside from those, a series of sharp signals with
weak intensity along 1700 cm-1 - 1900 cm-1.

Referring to the IR absorption frequencies table, the results show that the absorption
at the 3100 cm-1 indicates that it has aromatic rings with a C-H bond. Also, it also contains
C-C bonds.

An unknown sample (UNKNOWN A) also displayed the same spectrum, after

scanning, thus, it can be inferred that the compound is also toluene.
 Fig. 5. The spectra displayed by Infrared Spectrometer when it scanned
cyclohexanone(left) and UNKNOWN B compound (right).

Cyclohexanone. A drop of cyclohexanone, C5H12O was later examined. To have

consistent data, the same method was used to investigate the composition of
cyclohexanone. To do this effectively, Infrared spectroscopy was used to scan the drop of
the compound, which produced its own spectrum (shown in Fig. 5).

The spectrum displayed two spikes, one was moderately strong ranging from 3000
cm-1 down to 2800 cm-1, while the second was posed a stronger frequency ranging from
1780 cm-1 to 1650 cm-1. These results can be interpreted as to what composes the
compound.

With the first peak’s frequency and strength (3000 cm -1 - 2800 cm-1), it can be
inferred that cyclohexanone contains an alkane group (C-H) (literature value 2960-2850 cm-
1). In addition, the second peak indicates the presence of a ketone group (RC(=O)R), using

the data from the frequency from 1760 cm-1 to 1670 cm-1 (literature value 1760-1670 cm-1).
When UNKNOWN B was scanned by the same instrument, congruent results were
obtained.

The samples were distinguished from each other according to the different peaks
located at a specific range. This was accomplished using the method of Infrared
Spectroscopy, which provided the needed information about the given samples, in order to
match the unknown samples with the more familiar, known ones.The vibrations of the
molecules are critical to the interpretation of IR spectra (Stuart, 2015).

To summarize the data presented, refer to the Table 1:

 Sample Compounds IR Frequency Functional Group Functional
Peaks (cm-1) Bonds Detected Group

Hexane and Unknown 2850 - 2975 cm-1 C-H Alkane

Sample C

Cyclohexanol and 3400 - 3200 cm-1 & O-H & C-H Hydroxyl &
Unknown Sample D 2950 - 2800 cm-1 Alkane

Isoamyl alcohol and 3400 - 3100 cm-1 & O-H & C-H Hydroxyl &
Unkown Sample E 2950 - 2800 cm-1 Alkane

Toluene and Unknown 3100 - 2950 cm-1 & C-H & C=C Alkane &
Sample A 1600 - 1500 cm-1 Aromatic Ring

Cyclohexanone and 3000 - 2800 cm-1 & C-H & C=O Alkane &
Unknown Sample B 1780 - 1650 cm-1 Ketone

Table 1. The table showed the sample compounds with its corresponding IR frequency
peaks. The functional groups and bonds were also included according to its peaks.

The Cyclohexanol and Isoamyl alcohol, together with the Unknown E and D, showed
similar IR frequency peaks. This signifies identical functional bonds, O-H & C-H. This means
that the functional groups are Hydroxyl & Alkane group. On the other hand, the hexane,
toluene, and cyclohexane showed different peaks.

The Toluene and Unknown A exhibit 3100 - 2950 cm-1 & 1600 - 1500 cm-1 frequency
peaks. This suggests Alkane & Aromatic Ring with bonds C-H & C=C. The Cyclohexanone
and the hexane, along with its corresponding unknown samples, also contain Alkane
functional group. Lastly, the cyclohexane showed peaks between 3000 - 2800 cm-1 & 1780
- 1650 cm-1. This suggests additional Ketone functional group with bonds C=O.

Experimental

The infrared spectrophotometer was cleaned by wiping 5% ethanol to the sample

platform and it was dried afterwards. This is to make sure that the results may not be
affected following the cleaning of the machine before use. With the use of the computer
software, the Sample ID Icon was clicked and the name was changed according to the
assigned group number and solution. The background icon was clicked for calibration. This
is to ensure that the beam path is clear. After checking if it is free from any chemical
residues, the chemical sample, Toluene, was put the on the sample platform. The
adjustment knob was twisted until the needle tip touched the sample reservoir. The scan
icon was clicked subsequently and the spectrum showed on the computer screen. Other
samples, including the Cyclohexanol, Hexane, Cyclohexanol, and Isoamyl, were also tested
and measured the IR frequencies.
Figure 6. Basic components of IR spectrometer with vibrational frequency process

(Source:https://chem.libretexts.org/@api/deki/files/12713/Figure10.33.jpg?revision=1)

Conclusion

The spectra that the students obtained from the Infrared Spectroscopy were all in
lieu with the frequency table that was provided to the students. Each peak corresponded to
a functional group in accordance with its range. There were different intensities and signals
shown by the spectra of the samples. The table of frequency indicated the literature values
that were mentioned in the Results and Discussions. However, the students have noticed
that a slight mistake or difference in the manner of doing the spectroscopy can yield to a
relative big differences. They have noticed, as well, that the unknown compounds that were
given to them are similar to the known compounds that are given to other groups. That will
explain the relative similarities in the spectra of the unknown compounds to the known ones.

References

Chemistry LibreTexts. (2017). Infrared Spectroscopy. Retrieved from

https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_
Textbook_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistr
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Chemistry LibreTexts. (2017). Infrared Spectroscopy. Retrieved from

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistr
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IR Spectra: Tricks for Identifying the 5 Zones. (n.d.). Retrieved from

http://www.chem.ucla.edu/~harding/ec_tutorials/tutorial62.pdf

Stuart, B. (2015). Infrared Spectroscopy. Kirk-Othmer Encyclopedia of Chemical

Technology, 1-18. doi:10.1002/0471238961.0914061810151405.a01.pub